WO1990010686A1 - Procede de production d'huile isolante comprenant du dibenzylbenzene - Google Patents

Procede de production d'huile isolante comprenant du dibenzylbenzene Download PDF

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Publication number
WO1990010686A1
WO1990010686A1 PCT/JP1990/000295 JP9000295W WO9010686A1 WO 1990010686 A1 WO1990010686 A1 WO 1990010686A1 JP 9000295 W JP9000295 W JP 9000295W WO 9010686 A1 WO9010686 A1 WO 9010686A1
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WO
WIPO (PCT)
Prior art keywords
oil
impregnated
capacitor
zsm
reaction
Prior art date
Application number
PCT/JP1990/000295
Other languages
English (en)
Japanese (ja)
Inventor
Shigenobu Kawakami
Keiji Endo
Hideyuki Dohi
Atsushi Sato
Original Assignee
Nippon Petrochemicals Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Petrochemicals Co., Ltd. filed Critical Nippon Petrochemicals Co., Ltd.
Priority to EP90904422A priority Critical patent/EP0417308B1/fr
Priority to CA002028828A priority patent/CA2028828C/fr
Priority to DE69022339T priority patent/DE69022339T2/de
Publication of WO1990010686A1 publication Critical patent/WO1990010686A1/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G4/00—Fixed capacitors; Processes of their manufacture
    • H01G4/002—Details
    • H01G4/018—Dielectrics
    • H01G4/20—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06
    • H01G4/22—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06 impregnated
    • H01G4/221—Dielectrics using combinations of dielectrics from more than one of groups H01G4/02 - H01G4/06 impregnated characterised by the composition of the impregnant
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/06—Well-defined hydrocarbons aromatic
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
    • H01B3/22—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/16—Dielectric; Insulating oil or insulators
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/14—Electric or magnetic purposes
    • C10N2040/17—Electric or magnetic purposes for electric contacts

Definitions

  • the present invention relates to a method for producing an electrical insulating oil comprising dibenzylbenzenes.
  • the electric insulating oil produced according to the present invention is suitable as an impregnating oil for oil-impregnated electric equipment using at least a part of an insulator or a dielectric made of a plastic.
  • a further preferred device is an oil-impregnated capacitor, most preferably an oil-impregnated metallized plastic film capacitor.
  • the impregnated type MF capacitor has a higher withstand voltage than the dry type, and meets the requirements for miniaturization and lightening.
  • metallized films based on plastic films are particularly affected by impregnated oil.
  • base films made of impregnated oil Even if the dimensional change of the metal or the impregnation of the impregnating oil between the deposited metal layer and the base film layer occurs slightly, cracks may occur in the deposited metal layer, and in severe cases, the deposited metal layer may peel off. It often leads to dielectric breakdown. Therefore, MF capacitors have less effective electrical insulating oil.
  • MF components impregnated with aryl alkane such as benzil toluene or phenyloxyl luteane Capacitors have a remarkable decrease in their capacity during use, and their corona (partial) discharge characteristics are not always good.
  • the present invention uses a S i 0 2 / A 1 2 0 3 mode by Le ratio Tsu der 2 0 or more, and crystalline synthetic peptidase Orai preparative catalyst inlet of the main cavity consists of 1 0-membered oxygen ring,
  • An electric power comprising dibenzyl benzenes, characterized by reacting benzene or toluene with diphenylmethane or a derivative thereof at a reaction temperature of 170 to 400 ° C. It relates to a method for producing insulating oil.
  • ZSM A method for the production of xylene by the mutual disproportionation of toluene with the use of type 5 zeolite as a catalyst has already been disclosed (British Patent No. 1,463,33). 5 No. 9 and others). These are, of course, due to the transfer of the methyl group.
  • ZSM-5 Type Zee Light when dibenzirbenzenes are produced from toluene and diphenylmethane, if there is a transfer of methyl groups, toluene is present.
  • xylene is expected to form. The production of xylene consumes the corresponding amount of toluene, which lowers the yield of dibenzylbenzenes, which is not preferred. Therefore, ZSM-5 catalysts are not expected to be suitable for producing dibenzyl benzenes from toluene and diphenyl methane.
  • the present inventors have surprisingly found that despite the presence of toluene, the reaction proceeded without substantially producing xylene, and dibenzylbenzenes were formed. . In addition, a large number of substituted methyl nuclei such as methyl and dimethyl are generated in addition to dibenzylbenzene.
  • one of the raw materials used in the present invention is benzene or toluene. These may be mixed.
  • the other source is diphenylmethane or its methyl-substituted product.
  • the methyl substituent is specifically benzyltoluene or ditolumetane.
  • Diphenylmethane, benzyltoluene and ditolylmethane can be used as a mixture.
  • dibenzylbenzenes produced by the method of the present invention include dibenzylbenzene, as well as dibenzylbenzene dimethyene such as dibenzylbenzene and the like. And nucleus-substituted products.
  • reaction conditions of benzene or toluene and diphenylmethane or a methyl-substituted product thereof in the present invention are as follows.
  • the catalyst, a is S i 0 2 / A l 2 0 3 molar ratio of 2 0 or more
  • the main cavity is made of a crystalline synthetic aluminosilicate or zeolite having a 10-member oxygen ring.
  • a zeolite light include a synthetic zeolite of 2 SM-5 type in which the entrance of the main cavity is composed of a 10-membered oxygen ring, and a zeolite zeta lighter.
  • the zeolite of the present invention is characterized by comprising a 10-membered oxygen ring.
  • Conventional synthetic zeolites such as A-type zeolite, erionite, and off-letite, are 8-membered oxygen-ring-type small-pore zeolites, and include mordenite, X-type zeolite, and Y-type zeolite. And others are 12-membered oxygen ring type large pore zeolite.
  • Crystalline synthetic Zeorai preparative used in the present invention has the structural characteristics of input Ri mouth of the main air-dong is found or 1 0-membered oxygen ring, crystalline Si0 2 / Al 2 0 3 molar ratio is 2 0 or more Any synthetic aluminum silicate can be used.
  • ZSM-5 type synthetic zeolites such as ZSM-5, ZSM-11, ZSM-12, ZSM-22, ZSM-23, ZSM-35, ZSM-. Also known as 38, ZSM—48.
  • Each of these ZSM-5 type synthetic zeolites has a structural characteristic in which the entrance of the main cavity is composed of a 10-membered oxygen ring.
  • Particularly suitable combination The synthetic zeolite is ZSM-5.
  • the composition and production method of these ZSM-5 type zeolites are all described in the following patent publications.
  • ZSM-35 Japanese Patent Application Laid-Open No. Sho 53-144 550
  • Zeolite Printer 1 Japanese Patent Application Laid-Open No. 51-672299
  • Zeoryta Printer 3 Japanese Patent Application Laid-Open No. 51 - 6 7 2 9 synthesis
  • No. main cavity structural characteristics consisting of 1 0-membered oxygen ring generally has a high Si0 2 / Al 2 0 3 molar ratio, its value is usually 2 0 or more.
  • Si) 2 / Al 2 0 3 molar ratio is very high, for example, 1 6 0 0 or more such zero talent. Rye preparative also effective.
  • Si0 2 / Al 2 0 3 molar ratio uses Zeorai bets close to infinity.
  • the zeolite of “high silica” is also included in the definition of the present invention.
  • the Si0 2 / Al 2 0 3 molar ratio is measured by conventional analytical methods such as atomic absorption spectrometry. This ratio represents a value as close as possible to the ratio in the hard anion skeleton of the zeolite light crystal, and the ratio of cations in the binder or in the channel is reduced. Aluminum in other forms is excluded.
  • the structure in which the entrance of the main cavity consists of a 10-membered oxygen ring is usually confirmed by X-ray diffraction.
  • the synthetic zeolite of the type ZSM-5 which is preferable as the catalyst of the present invention, has a characteristic X-ray diffraction pattern (see the above-mentioned patent publication for details).
  • the 10-membered oxygen ring of the present invention can be defined as a synthetic zeolite having a control index of 1 to 12.
  • a specific method of measuring the control index is disclosed in Japanese Patent Application Laid-Open No. 56-133322. This index indicates the degree to which the pore structure of zeolite crystals controls the approach of molecules with larger cross-sectional areas than n-paraffins.
  • the measurement is carried out by adsorbing n-hexane and 3-methylpentane on zeolite under certain conditions, and calculating from the adsorbed amounts thereof.
  • Typical control indices are as follows.
  • a method for synthesizing 2SM-5 will be described.
  • the composition is in the range described in the above publication, and the reaction mixture is heated to perform hydrothermal synthesis. After the synthesis, the obtained crystals are calcined in the air to obtain Zeolite ZSM-5 catalyst. Iced tetrabrovir ammonium can also be synthesized in situ from n-bromoviramine and 1-bevirebromide in the reaction system.
  • the method using aluminum oxide has been described, but it has also been proposed to synthesize ZSM-5 that does not substantially contain an aluminum atom.
  • the zeolite used in the reaction contains, for example, sodium ions and other metals due to the reaction raw materials at the time of synthesis.
  • Alkaline earth metals such as calcium and magnesium as well as alkali metals such as Na and those ion-exchanged with trivalent metals can also be used.
  • crystalline synthetic aluminosilicate modified with boron, potassium, phosphorus, or these compounds ⁇ Zelite light, for example, ZSM-5 type Zelite light may also be used. It can.
  • These ion exchange or denaturation can be performed by a conventionally known method.
  • the crystalline synthetic zeolite of the present invention can contain various metals, but a so-called hydrogen-type zeolite obtained by exchanging metal ions with hydrogen ions is preferable for the method of the present invention.
  • a typical hydrated zeolite is prepared by heating a catalyst containing an organic cation at the time of preparing the catalyst under an inert atmosphere, for example, at 400 to 700 ° C for 1 hour, and then removing the ammonia. Ion exchange with mineral acid such as palladium salt or hydrochloric acid
  • the reaction temperature of the present invention is from 170 to 400 ° C, preferably from 200 to 350 ° C.
  • reaction temperature is lower than this range, the conversion of the raw material will be low. On the other hand, if the reaction temperature is higher than this range, side reactions such as formation of xylene occur, which is not preferable.
  • the reaction can be carried out in the gas phase, but in order to maintain the catalytic activity for a long time, it is appropriate to carry out the reaction in the liquid phase.
  • the gaseous phase must necessarily have a high reaction temperature, and if the reaction temperature is high, side reactions such as generation of xylene are likely to occur as described above. The reaction therefore takes place in the liquid phase.
  • reaction pressure In order to carry out the reaction in the liquid phase, it is desirable to set the reaction pressure to an appropriate pressure to keep the reaction phase in the liquid phase.
  • This pressure is usually selected from the range of normal pressure to 50 kg / cm 2 .
  • reaction type of the method of the present invention either a flow type or a batch type can be selected.
  • the reaction time is selected from the range of 0.5 to 50 hours according to the reaction temperature and other reaction conditions in the Knott's equation. If the reaction time is shorter than this range, the conversion will be lower. Further, if the reaction time is made unnecessarily long, the yield of dibenzylbenzenes is not improved, but rather, only a side reaction is caused, which is not preferable.
  • LHSV is 0.2 to 20; It is preferably from 0.5 to 10. If the LHSV is smaller than this, the number of side reactions increases, and the yield per hour decreases, which is not preferable. Conversely, if the LHSV becomes too large, the reaction does not proceed, and the reaction raw materials flow out of the system without reacting, which is not preferable.
  • the reaction mixture is usually 0 :! Up to 10% by weight, preferably 0.5 to 5% by weight of the catalyst may be used. If the catalyst concentration is lower than this, the reaction does not proceed. On the other hand, if the catalyst concentration is higher than this, the yield of the target compound is not always improved, and the use of a large amount of the catalyst is uneconomical.
  • ⁇ compound such as difunylmethane is 0.2 to 20 and preferably 0.5 to: I 0. . If the molar ratio is smaller than this, that is, if the amount of the monocyclic compound used relative to the bicyclic compound is small, the conversion of the raw material decreases, which is not preferable. Conversely, if the molar ratio is higher than the above range and a monocyclic compound is used in excess, the amount of dibenzylbenzenes produced per reaction is reduced, which is not preferable.
  • the unreacted monocyclic compound and unreacted bicyclic compound are separated, and the dibenzylbenzenes of the present invention can be obtained by a conventional method.
  • oil-impregnated electric equipment to which the electric insulating oil of the present invention is suitably impregnated examples include oil-impregnated electric equipment in which at least a part of an insulator or a dielectric is made of a plastic, for example, oil-impregnated electric equipment.
  • oil-impregnated electric equipment in which at least a part of an insulator or a dielectric is made of a plastic, for example, oil-impregnated electric equipment.
  • capacitors and oil impregnated cables are examples of the electric equipment to which the electric insulating oil of the present invention is suitably impregnated.
  • the above-mentioned oil-impregnated capacitor is formed by laminating a metal foil such as an aluminum foil as an electrode and a plastic film and winding it to form a capacitor element. It is something that is allowed.
  • conventional insulating paper can be used together with the plastic film.
  • the brass chips include polyolefins such as polyethylene, polypropylene, and polypentene, polyvinylidene vinylidene, and polyester. Of these plastics, the polirefin is particularly preferred.
  • the electrode may be formed on the film as a vapor-deposited metal layer, and such a capacitor is called an MF capacitor as described above.
  • the electric insulating oil of the present invention is particularly suitably used for this MF condenser.
  • the oil-impregnated cable is made by winding a metal conductor such as copper or aluminum with a plastic film and impregnating it with electric insulating oil in a usual manner.
  • the plastic include polyolefins such as polyethylene, polypropylene, and polypentene, polystyrene vinylidene, and polyester, and more preferably polyolefin. In this case, usually used in combination with insulating paper, composite film in which polyolefin is fused or bonded to insulating paper, or mixed paper made of polyolefin and pulp Use
  • the electric insulating oil obtained by the method of the present invention has a high boiling point. Despite this, it has relatively low viscosity and low pour point. Therefore, it can be suitably used as an electric insulating oil, and it can be used as a conventionally known electric insulating oil, for example, refined mineral oil, polyolefin such as polybutene, alkynolebenzene such as dodecyl benzene, etc.
  • Diaryl alkanes such as diphenylisolemetane, phenyltriluethane, phenyloxyliluethane, phenylisoprovirenilethane, saturated trimers of styrene, distylene
  • Trialkyl dialkanes such as xylene lene, dibenzyl toluene or trialkyl alkane, alkirubifenyl such as isobrovirbiphenyl, alkirnaphthalene such as diisopropylnaphthalene, etc.
  • it may be used in combination with one or more phthalic acid esters such as DOP in any proportion. It is Ru can.
  • the X-ray diffraction diagram and the like of this catalyst were the same as those described in the above-mentioned patent gazette (Japanese Patent Publication No. 46-104164). Further, the control index and the like also coincide, and therefore, the catalyst has a structural characteristic in which the entrance of the main cavity is composed of a 10-membered oxygen ring.
  • the oiled reaction solution was analyzed by gas chromatography to determine the composition of the reaction solution after a certain oil passage time. Table 1 shows the results.
  • Y-type zeolite has a low selectivity for dibenzylbenzenes and a significant decrease in activity. This decrease in activity was such that the activity could not be recovered by raising the reaction temperature from 180 to 260 ° C.
  • Example 2 After recovering the reaction solution of Example 1 and flushing benzene, toluene and xylene, the solution was distilled under reduced pressure to a boiling point of 350 to 420 ° C in terms of normal pressure. A distillate consisting of dibenzilbenzenes was recovered. At this time, partially precipitated crystals were separated by filtration.
  • Capacitor A metal-deposited polypropylene film having a width of 40 mm and a margin of 3 mm formed by vapor-depositing zinc on one side according to a conventional method was used. By winding the vapor-deposited film into a capacitor element and impregnating the recovered fraction, a capacitor having a capacity of about 5 yF (referred to as “capacitor A”) is obtained.
  • Capacitor A a capacitor having a capacity of about 5 yF
  • capacitor B For comparison, a similar capacitor element was impregnated with phenyloxysilylethane to obtain a capacitor for comparison (referred to as “capacitor B”).
  • a time-dependent change in the capacitance of each capacitor was measured by applying a potential of 120 V / ⁇ at 60 ° C. to each of the capacitors A and B.
  • the capacity of the capacitor ⁇ ⁇ hardly decreased even after 1000 hours.
  • the capacity of capacitor B was reduced by about 15% after 1000 hours from the capacity at the start.
  • the capacitor impregnated with benzyltoluene also showed a change in capacity after 1000 hours similar to that of capacitor B impregnated with phenylxylylethane.
  • the present invention provides a novel method for producing an electrically insulating oil. Further, the electric insulating oil of the present invention is most suitable as an impregnating oil for the MF capacitor.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Organic Insulating Materials (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Fixed Capacitors And Capacitor Manufacturing Machines (AREA)

Abstract

On produit une huile isolante comprenant des dibenzylbenzènes, indiquée pour l'imprégnation d'un condensateur à film plastique métallisé, en faisant réagir du benzène ou du toluène avec du diphénylméthane ou l'un de ses dérivés méthylés à une température comprise entre 170 et 400°C en présence d'un catalyseur à base de zéolite cristallin synthétique présentant un rapport molaire entre le SiO2 et l'Al2O3 égal ou supérieur à 20, dans lequel l'ouverture d'une cavité principale est constituée d'un anneau d'oxygène à dix éléments.
PCT/JP1990/000295 1989-03-07 1990-03-07 Procede de production d'huile isolante comprenant du dibenzylbenzene WO1990010686A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP90904422A EP0417308B1 (fr) 1989-03-07 1990-03-07 Procede de production d'huile isolante comprenant du dibenzylbenzene
CA002028828A CA2028828C (fr) 1989-03-07 1990-03-07 Methode de production d'une huile isolante contenant des dibenzylbenzenes
DE69022339T DE69022339T2 (de) 1989-03-07 1990-03-07 Verfahren zur herstellung eines dammenden öles enthaltend dibenzylbenzen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP1/54144 1989-03-07
JP1054144A JP2794444B2 (ja) 1989-03-07 1989-03-07 ジベンジルベンゼン類の製造方法

Publications (1)

Publication Number Publication Date
WO1990010686A1 true WO1990010686A1 (fr) 1990-09-20

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Application Number Title Priority Date Filing Date
PCT/JP1990/000295 WO1990010686A1 (fr) 1989-03-07 1990-03-07 Procede de production d'huile isolante comprenant du dibenzylbenzene

Country Status (6)

Country Link
US (1) US5107395A (fr)
EP (1) EP0417308B1 (fr)
JP (1) JP2794444B2 (fr)
CA (1) CA2028828C (fr)
DE (1) DE69022339T2 (fr)
WO (1) WO1990010686A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05159967A (ja) * 1991-12-10 1993-06-25 Nippon Petrochem Co Ltd 金属化プラスチックフィルムコンデンサー
US5719742A (en) * 1995-11-29 1998-02-17 Nippon Petrochemicals Co., Ltd. Metallized plastic film capacitor
US6585917B2 (en) 2001-04-12 2003-07-01 Cooper Industries, Inc. Dielectric fluid
HU224862B1 (en) * 2002-03-06 2006-03-28 Abo Mill Malomipari Rt Process for producing of rice by short cooking time
EP2089215B1 (fr) 2006-12-08 2015-02-18 3D Systems Incorporated Système de matériaux d'impression tridimensionnelle
US7968626B2 (en) * 2007-02-22 2011-06-28 Z Corporation Three dimensional printing material system and method using plasticizer-assisted sintering
CN113583737B (zh) * 2021-05-28 2022-05-20 广西大学 一种利用纳米SiO2改性的棕榈绝缘油的制备方法

Citations (8)

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US3481997A (en) * 1968-04-25 1969-12-02 Sun Oil Co Intermolecular condensation of aromatic compounds
JPS4895599A (fr) * 1972-03-17 1973-12-07
JPS4914320B1 (fr) * 1969-03-31 1974-04-06
JPS4941634B1 (fr) * 1970-12-12 1974-11-09
JPS49135199A (fr) * 1973-05-04 1974-12-26
GB1579679A (en) * 1976-07-16 1980-11-19 British Petroleum Co Electro-erosion process using dielectric liquids
JPH06116410A (ja) * 1992-10-02 1994-04-26 Sumitomo Metal Ind Ltd 熱硬化性樹脂プリプレグ及び積層材
JPH06151704A (ja) * 1992-11-11 1994-05-31 Mitsubishi Electric Corp 半導体装置及び配置配線装置

Family Cites Families (6)

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Publication number Priority date Publication date Assignee Title
JPS6116410A (ja) * 1984-06-29 1986-01-24 日本石油化学株式会社 電気絶縁油
JPH06101245B2 (ja) * 1984-08-03 1994-12-12 日本石油化学株式会社 電気絶縁油の製造方法
JPS6151704A (ja) * 1984-08-18 1986-03-14 日本石油化学株式会社 電気絶縁油
US4744000A (en) * 1987-07-29 1988-05-10 Cooper Industries, Inc. Electrical capacitor having improved dielectric system
JPH0788319B2 (ja) * 1987-09-09 1995-09-27 日本石油化学株式会社 ｍ−ベンジルトルエンの製造方法
JPH0810566B2 (ja) * 1988-03-09 1996-01-31 日本石油化学株式会社 改良された留分からなる電気絶縁油

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3481997A (en) * 1968-04-25 1969-12-02 Sun Oil Co Intermolecular condensation of aromatic compounds
JPS4914320B1 (fr) * 1969-03-31 1974-04-06
JPS4941634B1 (fr) * 1970-12-12 1974-11-09
JPS4895599A (fr) * 1972-03-17 1973-12-07
JPS49135199A (fr) * 1973-05-04 1974-12-26
GB1579679A (en) * 1976-07-16 1980-11-19 British Petroleum Co Electro-erosion process using dielectric liquids
JPH06116410A (ja) * 1992-10-02 1994-04-26 Sumitomo Metal Ind Ltd 熱硬化性樹脂プリプレグ及び積層材
JPH06151704A (ja) * 1992-11-11 1994-05-31 Mitsubishi Electric Corp 半導体装置及び配置配線装置

Also Published As

Publication number Publication date
DE69022339D1 (de) 1995-10-19
JP2794444B2 (ja) 1998-09-03
CA2028828C (fr) 2000-11-21
DE69022339T2 (de) 1996-05-09
EP0417308A4 (en) 1991-09-25
US5107395A (en) 1992-04-21
EP0417308A1 (fr) 1991-03-20
JPH02233624A (ja) 1990-09-17
CA2028828A1 (fr) 1990-09-08
EP0417308B1 (fr) 1995-09-13

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